Anti-infective agents and uses thereof

Inactive Publication Date: 2014-04-01
ABBVIE INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The invention has benefits for people who work in the field of medical technology. The patent explains how it can be used to improve the accuracy and efficiency of medical diagnostic tools.

Problems solved by technology

An HCV infection can cause liver inflammation (hepatitis) that is often asymptomatic, but ensuing chronic hepatitis can result in cirrhosis of the liver (fibrotic scarring of the liver), liver cancer, and / or liver failure.
There is a small chance of clearing the virus spontaneously, but the majority of patients with chronic hepatitis C will not clear it without treatment.
Treatment may be physically demanding, particularly for those with prior history of drug or alcohol abuse, because both interferon and ribavirin have numerous side effects.
Common interferon-associated side effects include flu-like symptoms, extreme fatigue, nausea, loss of appetite, thyroid problems, high blood sugar, hair loss, and skin reactions at the injection site.

Method used

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  • Anti-infective agents and uses thereof
  • Anti-infective agents and uses thereof
  • Anti-infective agents and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

examples

[1181]The following examples are merely illustrative, and not limiting to this disclosure in any way.

example a

Preparation of (E)-N-(3-tert-butyl-5-iodo-4-methoxyphenylcarbamoyl)-3-methoxy acrylamide

[1182]

Part A. Preparation of 2-tert-butyl-4-nitrophenol

[1183]To a vigorously stirred solution of 2-tert-butylphenol (10 g, 66.6 mmol) in heptane (67 ml) was added at a fast drip a solution of 70% nitric acid (4.25 ml, 66.6 mmol) diluted with water (4.25 ml). The resulting dark red / brown mixture was stirred vigorously for 2 h. The suspended solid was collected by filtration washed with hexane (300 mL), water (200 mL) and once again with hexane (200 mL) to give a cocoa colored powder that was dried to constant mass (4.65 g, 35.6%).

Part B. Preparation of 2-tert-butyl-6-iodo-4-nitrophenol

[1184]To the product from Part A (4.5 g, 23.05 mmol) dissolved in MeOH (120 ml) and water (30 mL) was added iodine monochloride (1.155 ml, 23.05 mmol) drop wise over a period of 10 min. The mixture was stirred for 2 h and diluted into 1 L of water and allowed to stand overnight. The solid material was collected by fi...

example b

Preparation of 1-(3-tert-butyl-5-iodo-4-methoxyphenyl)dihydropyrimidine-2,4(1H,3H)-dione

[1188]

[1189]To a suspension of the product from Example A (2.46 g, 5.69 mmol) in ethanol (50 ml) was added a solution of 5.5 mL of H2SO4 in 50 mL water and the mixture was heated at 110° C. for 2.5 h to give a clear solution. The solution was cooled and diluted with 50 mL of water while stirring to give an off-white solid that was collected by filtration, washed with water and dried (2.06 g, 90%).

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Abstract

This invention relates to: (a) compounds and salts thereof that, inter alia, inhibit HCV; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) kits comprising such compounds, salts, and compositions.

Description

CROSS-REFERENCE TO RELATED PATENT APPLICATIONS[0001]This patent application is a continuation application of U.S. patent application Ser. No. 12 / 725,689 (filed Mar. 17, 2010) which is a continuation of International Patent Application No. PCT / US2008 / 076576 (filed Sep. 17, 2008), which, in turn, claims priority to U.S. Provisional Patent Application No. 60 / 972,877 (filed Sep. 17, 2007) and U.S. Provisional Patent Application No. 61 / 096,791 (filed Sep. 13, 2008). The entire text of those applications is incorporated by reference into this application.FIELD OF THE INVENTION[0002]This invention is directed to: (a) compounds and salts thereof that, inter alia, are useful as hepatitis C virus (HCV) inhibitors; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) ki...

Claims

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Application Information

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IPC IPC(8): C07D239/54
CPCC07D239/22C07D401/10C07D403/10C07D409/10C07D413/10C07D417/10C07D239/54A61K31/513A61K31/5377C07D405/10C07D417/14A61P1/16A61P31/12A61P31/14A61P43/00
InventorWAGNER, ROLFKATI, WARREN M.LIU, DACHUNLIU, YAYALONGENECKER, KENTON L.MARING, CLARENCE J.PRATT, JOHN K.ROCKWAY, TODD W.STEWART, KENT D.TUFANO, MICHAEL D.
OwnerABBVIE INC